You ever know that one kid in school who just couldn’t stay out of trouble? The one who had a permanent seat in detention and somehow seemed proud of it? Maybe you were that kid. Now think about them for a second—where do you think they ended up? Jail? Maybe running some shady business out of their mom’s basement? Or maybe they cleaned up their act and became a motivational speaker.

Well, in today’s episode, I’m going to tell you about a guy who definitely didn’t clean up his act. Hank Vaughan. Now, Hank wasn’t exactly what you’d call a household name like Billy the Kid or Jesse James, but let me tell you, this guy lived just as wild of a life—maybe even wilder. He’s Oregon’s most infamous horse rustler, gunfighter, and all-around menace to society. If Hollywood ever runs out of superhero reboots, Hank Vaughan’s story would be a goldmine.

So grab a drink, settle in, and let’s dive into the absolute madness that was Hank Vaughan’s life.

Hank’s Early Days: A Farm Boy with Other Plans

Hank Vaughan was born in 1849 in Oregon. Now, while most kids in that era would have just helped out on the family farm and maybe dreamed of something more, Hank? He was already bored of life before he hit puberty. His dad and uncles had skipped town to try their luck in the California Gold Rush, leaving Hank and the rest of the family to run their little farm.

And I know what you’re thinking—“Oh, a farm boy, so peaceful.” Nope. Hank hated it. He wasn’t exactly cut out for farming life. He wanted adventure, chaos, something more... exciting. You know, the kind of excitement that lands you in prison or worse.

But let’s be real for a second: being a 13-year-old kid running a horse trading business wasn’t exactly easy. People took advantage of him, and Hank? Well, let’s just say he wasn’t going to take it lying down.

The First Gunshot: Hank and His Liquid Courage

Now, here’s where the trouble really started.

When Hank was 15 years old, he sold a horse to William Headspot on credit. Headspot, of course, was a gambler who never intended to pay him back. Classic, right? When Hank finally went to collect, Headspot gave him a bunch of excuses—said he lost the money in a poker game. Hank, being the mature and rational 15-year-old he was, decided the best course of action was to head straight to the saloon for some liquid courage.

Picture this: a 15-year-old kid, sitting at the bar, throwing back whiskey like he’s 40. He’s fuming, working himself up. After a couple of drinks, Hank stormed out to confront Headspot again. And what does Headspot do? He mocks him. Says the horse was stolen property to begin with.

Now, I don’t know about you, but if someone said that to me when I was a drunk teenager, I’d probably be doing some stupid stuff too. So Hank pulls out his colt revolver, shoots at Headspot, and grazes the top of his head. Yeah, that could’ve been way worse, but still, Hank had officially made his grand entrance into the world of outlaws.

Naturally, Hank ran for it, hid out for about a week, but he wasn’t exactly good at the whole "staying out of sight" thing, so the law caught up to him pretty quick.

The Army, a Brief Detour in Outlaw Life

Now, at this point, you’re probably thinking, “Wow, this kid’s done for.” Well, not quite. Hank’s father made a deal with the judge: if Hank joined the 1st Oregon Volunteer Infantry, they’d let him off the hook. Maybe some time in the army would do him good, right? Wrong.

Hank lasted all of six weeks before being dishonorably discharged. Army life didn’t suit him any better than farm life did, and you can only imagine how thrilled his superiors were to kick him out. Honestly, this should’ve been a clue that maybe he wasn’t cut out for the straight-and-narrow path.

Becoming an Outlaw: Horse Rustling with Dick Bunton

Once Hank was back in civilian life, he hooked up with Dick Bunton, another outlaw with big dreams of horse thievery. The two set their sights on Idaho Territory, where horses were selling for $200 a head. Back then, that was more money than a cowboy could make in a year. So naturally, they got to work.

On their way to Idaho, they started stealing horses, because, you know, why pay for them when you can just take them? But of course, they weren’t exactly subtle about it, and it didn’t take long for the sheriff of Umatilla County to catch wind of their little operation.

One night, while they were camped out, the sheriff and his deputy tracked them down. And like in all good Western stories, instead of sneaking up and grabbing them, they shout, “Throw up your hands!”

Yeah, bad move.

In seconds, Hank and Dick were firing back, and within moments, Dick was dead, the deputy was dead, the sheriff was unconscious and close to death and Hank? Well, Hank was bleeding from a gunshot wound to the head but somehow still alive. And get this, he managed to escape. Of course, he didn’t get far—he was caught later, but his reputation was cemented.

A Near Lynching and a Hero’s Entrance

Now, at this point, the locals were done with Hank. They were ready to take justice into their own hands. A mob formed outside the jail, and they were prepared to lynch him. And honestly, this could have been it for Hank Vaughan. But here’s where things take a cinematic turn. One man—guns drawn—stood in front of the mob and declared Hank would get a fair trial, or else.

The mob grumbled and muttered but ultimately backed off. Hank lived to see another day.

Prison Life: Marching to Salem

Hank was sentenced to life in prison, but don’t think this is where the story ends. Nope, prison was just another chapter in the Hank Vaughan saga. In 1866, Hank and other prisoners were chained together and marched through the mud down to Salem to help build the new prison.

Now picture this: it’s a week-long march, crowds coming out to watch these chained-up criminals trudging along through the mud—it was practically entertainment for the townsfolk. And once they got there? They had to help build the very walls that would keep them locked up.

While in prison, Hank was forced to attend school. Yeah, that’s right—Hank Vaughan, notorious outlaw, had to hit the books. And surprisingly, he did well. But let’s be real, he was also getting an advanced degree in crime from the other inmates.

Eventually, his family petitioned for his release, claiming that Hank thought he was being robbed the night of the shootout. The governor of Oregon agreed, and Hank was pardoned.

Hank, The Horse Rustler

After Hank got out of prison he moved from town to town, eventually getting hitched 3 times. Hank lived two lives. One where he was an honest horse broker and one where he was a horse thief.

He didn’t just steal horses, he had a whole system. See, back in those days, there weren’t a lot of fences out in the open range. Ranchers would drive cattle and horses across long distances, and a few stragglers would inevitably get left behind.

Hank was always conveniently nearby to "rescue" these poor lost animals—or, more accurately, snatch them up and claim them as his own. He wasn’t dumb about it, either. Hank had several hideouts, where he’d take the stolen horses and keep them out of sight, far away from any trails where someone might recognize the brand.

Here’s the really clever part: he’d wait until the scars from the original brand healed over, and then he’d rebrand them with his own mark. This way, when he sold them, no one was the wiser.

But it gets even better. Hank’s third wife, a Native woman, helped him hide the horses right out in the open. How? They’d keep the stolen livestock on reservation land, where the law couldn’t touch them. This was like the Wild West version of hiding a stolen car in a garage to dodge the repo man.

With this system, Hank managed to make a small fortune. He’d operate an honest business by day, selling horses, and then by night, he was a full-blown horse thief. It was a perfect setup, and Hank was living the good life—well, as good as it gets when you're constantly dodging the law.

The Pilot Rock Jump: Hank’s Leap of Legend

So here’s where the legend of Hank Vaughan really takes off. In 1881, Hank was in Pilot Rock, Oregon, minding his own business—or, well, as much as Hank ever did. A posse accused him of stealing livestock, and instead of sticking around to clear his name, Hank jumped on his horse and bolted.

But here’s the wild part.

Hank didn’t just ride out of town—he rode his horse straight to the top of the bluffs there and when he reached the top, Hank did what no one expected—he jumped. That’s right—Hank and his horse leapt off the cliff.

The posse, in hot pursuit, made it to the top and peered over, fully expecting to see Hank and his horse splattered across the rocks below. But nope. Instead, they see Hank and his horse galloping away in the distance. As if gravity just didn’t apply to him. And what did Hank do next? He circled right back to town, strolled into the saloon, and finished his drink. The same one he left in the middle of when the posse came after him.

The Missouri Duel: A Standoff with a Twist

Now, if you thought jumping off cliffs was wild, just wait until you hear about the Missouri Duel.

Later in 1881, Hank found himself in Prineville, Oregon. He had a feeling there was a vigilante group plotting to take him down, so he tried to eavesdrop on their meeting in a local saloon. At one point, he sat down for a poker game with a guy named Charlie Long, but nothing much happened—yet.

Later that same day, Hank met Charlie again at another bar. Feeling a little generous, Hank offered to buy Charlie a drink. But Charlie? Charlie refused. And if you know anything about Hank, you’ll know he didn’t take too kindly to insults. Hank, not one to let things go, challenged Charlie to a Missouri Duel.

Now, a Missouri Duel isn’t your average duel. Both men hold onto the same handkerchief with one hand, and with the other hand, they fire point-blank at each other. No backing down, no room to hide.

Charlie fired first, grazing the top of Hank’s head, blood streaming down Hank’s face. But that didn’t faze him. Hank, wild-eyed and laughing like a maniac, fired back. They kept going, round after round, with Hank whooping and hollering like it was the best night of his life. At one point, Charlie had Hank pinned down, his revolver pressed against Hank’s forehead. And just when it looked like it was over for Hank? Click. Charlie was out of bullets.

Hank, once again, walked away alive, though not without a few new scars to add to his growing collection.

The Train Robbery: A Rare Heroic Moment

Believe it or not, Hank wasn’t always causing chaos. Sometimes, he was the hero—even if it was accidental.

Woken up from his nap by the commotion, Hank grabbed his gun and started firing. One of the robbers dropped dead, and the other two jumped off the train to escape. For his bravery, Hank was given a lifetime pass on the Northern Pacific Railroad. Because who better to stop a robbery than an outlaw who knows the ropes?

Terrorizing the Town: Hank the Practical Joker

Now, if there’s one thing Hank loved as much as stealing horses, it was pulling pranks—the kind of pranks that would probably get you arrested today.

One of his favorite tricks? Shooting at people’s feet and yelling, “Dance, varmint!” just like in the cartoons. And if that didn’t do the trick, he’d step it up a notch. If Hank didn’t get his way at a bar, he’d shoot out the windows, and if he was feeling extra ornery, he’d ride his horse into the saloon and start shooting bottles off the shelves until someone handed him a drink. This wasn’t a one-time thing either—this was Hank Vaughan’s idea of a good time.

But here’s the kicker: the next day, Hank would sober up and ride back into town. He’d pay for every single thing he’d broken, acting like it was just a normal part of the bar tab. People didn’t even bother getting mad anymore. That was just Hank being Hank.

The Final Ride: Hank’s Tragic End

For all his craziness, Hank’s life didn’t end in a shootout or at the gallows like you might expect. It ended in a tragic accident.

In May of 1893, while riding into Pendleton, Hank was showing off his famous horse-riding stunts. Galloping down the street, Hank’s horse suddenly slipped in the mud, throwing him headfirst into a pole. The impact was brutal—his skull was fractured, and his eye popped out of its socket. It was a horrifying sight.

Hank was taken to a boarding house, where he drifted in and out of consciousness. His family brought him his pet monkey—yes, you heard that right, Hank Vaughan had a pet monkey—and tried to make him comfortable. In one of the strangest twists of this story, Charlie Long, the man from the Missouri Duel, came to visit Hank on his deathbed. He even brought flowers, saying he held no grudge against him. Somehow, their insane duel was water under the bridge.

Sadly, Hank died on June 15, 1893, at the age of 44.

So that’s the life of Hank Vaughan—a man who lived like he had nothing to lose, loved his whiskey, his horses, and a good brawl. He wasn’t the most famous outlaw, but I’d argue he lived one of the wildest lives the West has ever seen. If you enjoyed this story, make sure to sign up for my email list to be notified when I post a new episode. This podcast as all my others are available in video form on YouTube and Rumble, in audio form on all the main podcast platforms like Spotify and Apple Podcasts and in article form on my website.